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Identification
Name Ergocalciferol
Accession Number DB00153 (APRD00426, NUTR00005)
Type small molecule
Groups approved, nutraceutical
Description

Ergocalciferol (Vitamin D2) is a derivative of ergosterol formed by ultraviolet rays breaking of the C9-C10 bond. It differs from cholecalciferol in having a double bond between C22 and C23 and a methyl group at C24. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Synthetic Vitamin D
Vitamin D2
Salts Not Available
Brand names
Name Company
Buco-D
Calciferol
Calciferon 2
Condacaps
Condocaps
Condol
Crtron
Crystallina
D-Arthin
D-Tracetten
Daral
Davitamon D
Davitin
De-Rat Concentrate
Decaps
Dee-Osterol
Dee-Ron
Dee-Ronal
Dee-Roual
Deltalin
Deratol
Detalup
Diactol
Divit Urto
Drisdol
Ercalciol
Ergorone
Ergosterol Activated
Ergosterol, Irradiated
Ertron
Fortodyl
Geltabs
Hi-Deratol
Infron
Metadee
Mulsiferol
Mykostin
Novovitamin-D
Oleovitamin D
Oleovitamin D, Synthetic
Oleovitamin D2
Ostelin
Radiostol
Radstein
Radsterin
Rodine C
Shock-Ferol
Shock-Ferol Sterogyl
Sterogyl
Uvesterol-D
Vio-D
Viostdrol
Viosterol
Viosterol in Oil
Vitavel-D
First Prev Next Last
Brand mixtures
Brand Name Ingredients
Calcimate Plus Calcium, Potassium, Magnesium and Vitamin D Calcium (Calcium Citrate, Calcium Malate) + Magnesium (Magnesium Oxide) + Potassium (Potassium Chloride) + Vitamin D2 (Ergocalciferol)
Calcium and Magnesium Citrate with Vitamin D Calcium (Calcium Citrate) + Magnesium (Magnesium Citrate) + Vitamin D (Ergocalciferol)
Calcium Magnesium 2:1 Tablets with Vitamin D Calcium (Calcium Citrate) + Magnesium (Magnesium Oxide) + Vitamin D2 (Ergocalciferol)
Centrum 8409 Beta-Carotene + Biotin + Chromium (Chromic Chloride) + Copper (Cupric Oxide) + D-Pantothenic Acid (Calcium D-Pantothenate) + Folic Acid + Iodine (Potassium Iodide) + Iron (Ferronyl) + Manganese (Manganese Sulfate) + Molybdenum (Sodium Molybdate) + Nicotinamide + Vitamin a (Vitamin a Acetate) + Vitamin B1 (Thiamine Mononitrate) + Vitamin B12 (Cyanocobalamin) + Vitamin B2 (Riboflavin) + Vitamin B6 (Pyridoxine Hydrochloride) + Vitamin C (Ascorbic Acid) + Vitamin D2 (Ergocalciferol) + Vitamin E (Vitamin E Acetate) + Vitamin K1 (Phytonadione) + Zinc (Zinc Oxide)
Insur-All Vitamin Supplement Biotin + Choline Bitartrate + D-Pantothenic Acid + Inositol + Nicotinamide + Vitamin a (Vitamin a Acetate) + Vitamin B1 (Thiamine Hydrochloride) + Vitamin B12 (Cyanocobalamin) + Vitamin B2 + Vitamin B6 (Pyridoxine Hydrochloride) + Vitamin C + Vitamin D (Ergocalciferol) + Vitamin E (Dl-Alpha Tocopheryl Acetate)
Mega Halibut Liver Oil Vitamin a (Halibut Liver Oil) + Vitamin D (Ergocalciferol)
Msb Essentials Beta-Carotene + Biotin + Calcium (Calcium Citrate) + Choline Dihydrogen Citrate + Chromium (Chromic Chloride) + D-Pantothenic Acid (Calcium D-Pantothenate) + Folic Acid + Inositol + Iodine (Potassium Iodide) + Iron (Ferrous Fumarate) + Magnesium (Magnesium Citrate) + Manganese (Manganese Hvp Chelate) + Methionine + Molybdenum (Sodium Molybdate) + Nicotinamide + Nicotinic Acid + Potassium (Potassium Citrate) + Selenium (Selenium Hvp Chelate) + Vitamin a (Vitamin a Acetate) + Vitamin B1 (Thiamine Hydrochloride) + Vitamin B12 + Vitamin B2 (Riboflavin-5-Phosphate) + Vitamin B6 (Pyridoxine Hydrochloride) + Vitamin C + Vitamin D (Ergocalciferol) + Vitamin E (D-Alpha Tocopherol) + Zinc (Zinc Chloride)
Pre-Natal Beta-Carotene (Provitamin a) + Biotin + Calcium (Calcium Citrate, Calcium Carbonate) + Chromium (Chromium Hvp Chelate) + Copper (Copper Hvp Chelate) + D-Pantothenic Acid (Calcium D-Pantothenate) + Folic Acid + Iodine (Potassium Iodide) + Iron (Iron Citrate) + Magnesium (Magnesium Hvp Chelate) + Manganese (Manganese Hvp Chelate) + Molybdenum (Molybdenum Hvp Chelate) + Nicotinamide + Potassium (Potassium Citrate) + Selenium (Selenium Hvp Chelate) + Silicon (Silicon Dioxide) + Vitamin a (Vitamin a Palmitate) + Vitamin B1 (Thiamine Hydrochloride) + Vitamin B12 (Cyanocobalamin) + Vitamin B2 (Riboflavin Hydrochloride, Riboflavin-5-Phosphate) + Vitamin B6 (Pyridoxine Hydrochloride, Pyridoxine 5' Phosphate) + Vitamin C (Calcium Ascorbate) + Vitamin D2 (Ergocalciferol) + Vitamin E (D-Alpha Tocopheryl Acid Succinate) + Zinc (Zinc Hvp Chelate)
Super Thera-M Beta-Carotene (Provitamin a) + Biotin + Calcium (Calcium Phosphate (Dibasic)) + Chloride (Potassium Chloride) + Chromium (Chromic Chloride) + Copper (Cupric Sulfate) + D-Pantothenic Acid (Calcium D-Pantothenate) + Folic Acid + Iodine (Potassium Iodide, Kelp) + Iron (Ferrous Fumarate) + Magnesium (Magnesium Oxide) + Manganese (Manganese Sulfate) + Molybdenum (Sodium Molybdate) + Nicotinic Acid (Nicotinamide) + Phosphorus (Calcium Phosphate (Dibasic)) + Potassium (Potassium Chloride) + Selenium (Sodium Selenate) + Vitamin a (Vitamin a Palmitate) + Vitamin B1 (Thiamine Mononitrate) + Vitamin B12 (Cyanocobalamin) + Vitamin B2 (Riboflavin) + Vitamin B6 (Pyridoxine Hydrochloride) + Vitamin C (Ascorbic Acid) + Vitamin D2 (Ergocalciferol) + Vitamin E (Dl-Alpha Tocopheryl Acetate) + Zinc (Zinc Sulfate)
Timed Release Multi Vitamin with Chelated Minerals Beta-Carotene (Provitamin a) + Biotin + Calcium (Calcium Hvp Chelate, Calcium Phosphate (Tribasic)) + Choline Bitartrate + Chromium (Chromium Hvp Chelate) + Copper (Copper Gluconate) + D-Pantothenic Acid (Calcium D-Pantothenate) + Dl-Methionine + Folic Acid + Inositol + Iodine (Potassium Iodide, Kelp) + Iron (Iron Hvp Chelate, Ferrous Fumarate) + Magnesium (Magnesium Oxide, Magnesium Hvp Chelate) + Manganese (Manganese Hvp Chelate) + Nicotinamide + Potassium (Potassium Chloride, Potassium Citrate) + Selenium (Selenium Hvp Chelate) + Vitamin B1 (Thiamine Hydrochloride) + Vitamin B2 (Riboflavin) + Vitamin B6 (Pyridoxine Hydrochloride) + Vitamin C (Ascorbic Acid) + Vitamin D (Ergocalciferol) + Vitamin E (D-Alpha Tocopheryl Acetate) + Zinc (Zinc Hvp Chelate)
Categories
  • Essential Vitamin
  • Antihypocalcemic Agents
  • Antihypoparathyroid Agents
  • Vitamins (Vitamin D)
  • Bone Density Conservation Agents
  • Vitamins
CAS number 50-14-6
Weight Average: 396.6484
Monoisotopic: 396.33921603
Chemical Formula C28H44O
InChI Key InChIKey=MECHNRXZTMCUDQ-RKHKHRCZSA-N
InChI
InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1
Plain Text
IUPAC Name
(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
SMILES
CC(C)[C@@H](C)\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C
Plain Text
Mass Spec show (9.78 KB)
Taxonomy
Kingdom Organic
Classes
  • Steroids and Steroid Derivatives
Substructures
  • Steroids and Steroid Derivatives
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Isoprenes
  • Alcohols and Polyols
Pharmacology
Indication For use in the management of hypocalcemia and its clinical manifestations in patients with hypoparathyroidism, as well as for the treatment of familial hypophosphatemia (vitamin D resistant rickets). This drug has also been used in the treatment of nutritional rickets or osteomalacia, vitamin D dependent rickets, rickets or osteomalacia secondary to long-term high dose anticonvulsant therapy, early renal osteodystrophy, osteoporosis (in conjunction with calcium), and hypophosphatemia associated with Fanconi syndrome (with treatment of acidosis).
Pharmacodynamics Ergoalcifediol (Vitamin D2) is a fat soluble steroid hormone precursor of vitamin D. The principal biologic function of vitamin D is the maintenance of normal levels of serum calcium and phosphorus in the bloodstream by enhancing the efficacy of the small intestine to absorb these minerals from the diet. Cholecalciferol is synthesized within our bodies naturally, but if UV exposure is inadequate or the metabolism of cholecalciferol is abnormal, then an exogenous source is required. Vitamin D2 is converted to 25-hydroxyvitamin D (25OHD) in the liver, and then to the active form, 1,25-dihydroxyvitamin D (1,25(OH)2D), in the kidney. Once transformed, it binds to the vitamin D receptor, which leads to a variety of regulatory roles. Vitamin D plays an important role in maintaining calcium balance and in the regulation of parathyroid hormone (PTH). It promotes renal reabsorption of calcium, increases intestinal absorption of calcium and phosphorus, and increases calcium and phosphorus mobilization from bone to plasma. Very few foods naturally contain vitamin D. Sources that contain the vitamin include fatty fish, the liver and fat of aquatic mammals (e.g., seals, polar bears), and eggs from chickens fed vitamin D-fortified feed. As such, many countries have instituted policies to fortify certain foods with vitamin D to compensate for the potentially low exposures of skin to sunlight. Vitamin D deficiency results in inadequate mineralization of bone or compensatory skeletal demineralization and causes decreased ionized calcium concentrations in blood and a resultant increase in the production and secretion of PTH. Increase in PTH stimulates the mobilization of skeletal calcium, inhibits renal excretion of calcium, and stimulates renal excretion of phosphorus. This results in normal fasting serum calcium concentrations and low or near-normal serum phosphorus. The enhanced mobilization of skeletal calcium induced by this secondary hyperparathyroidism leads porotic bone.
Mechanism of action Activated ergocalciferol increases serum calcium and phosphate concentrations, primarily by increasing intestinal absorption of calcium and phosphate through binding to a specific receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through formation of a calcium-binding protein. 25-hydroxyergocalciferol is the intermediary metabolite of ergocalciferol. Although this metabolite exhibits 2–5 times more activity than unactivated ergocalciferol in curing rickets and inducing calcium absorption and mobilization (from bone) in animals, this increased activity is still insufficient to affect these functions at physiologic concentrations. Activated ergocalciferol stimulate resorption of bone and are required for normal mineralization of bone. Physiological doses of ergocalciferol also promotes calcium reabsorption by the kidneys, but the significance of this effect is not known.
Absorption Readily absorbed from small intestine (proximal or distal), requires presence of bile salts.
Volume of distribution Not Available
Protein binding >99.8%
Metabolism Within the liver, ergocalciferol is hydroxylated to ercalcidiol (25-hydroxyergocalciferol) by the enzyme 25-hydroxylase. Within the kidney, ercalcidiol serves as a substrate for 1-alpha-hydroxylase, yielding ercalcitriol (1,25-dihydroxyergocalciferol), the biologically active form of vitamin D2.
Route of elimination Not Available
Half life 19 to 48 hours (however, stored in fat deposits in body for prolonged periods).
Clearance Not Available
Toxicity LD50 = 23.7 mg/kg (Orally in mice); LD50 = 10 mg/kg (Orally in rats ); Nausea, vomiting and diarrhea, weight loss, irritability, weakness, fatigue, lassitude, and headache.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
  • Sanofi aventis us llc
  • Orit laboratories llc
  • Sigmapharm laboratories llc
  • Strides arcolab ltd
  • Sun pharmaceutical industries inc
  • Banner pharmacaps inc
  • Chase chemical co lp
  • Everylife
  • Impax laboratories inc
  • Lannett co inc
  • Vitarine pharmaceuticals inc
  • West ward pharmaceutical corp
Packagers
Dosage forms
Form Route Strength
Capsule Oral
Prices
Unit description Cost Unit
Ergocalciferol powder 234.4 USD g
Doral 15 mg tablet 3.41 USD tablet
Doral 7.5 mg tablet 3.37 USD tablet
Drisdol 50000 unit capsule 2.34 USD capsule
Drisdol 8288 unit/ml Liquid 0.48 USD ml
Vitamin d 400 unit softgel 0.04 USD softgel capsule
Longs vitamin d 400 unit tablet 0.03 USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 116.5 °C PhysProp
water solubility 50 mg/L TOMLIN,C (1994)
logP 7.3 Not Available
Predicted Properties
Property Value Source
water solubility 4.33e-04 g/l ALOGPS
logP 7.59 ALOGPS
logP 7.05 ChemAxon
logS -6 ALOGPS
pKa (strongest acidic) 18.38 ChemAxon
pKa (strongest basic) -1.3 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 20.23 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 128.89 ChemAxon
polarizability 50.73 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. DeLuca HF: Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr. 2004 Dec;80(6 Suppl):1689S-96S. Pubmed
External Links
Resource Link
KEGG Drug D00187 Link_out
KEGG Compound C05441 Link_out
PubChem Compound 5280793 Link_out
PubChem Substance 46505053 Link_out
ChemSpider 4444351 Link_out
ChEBI 28934 Link_out
ChEMBL 28934 Link_out
Therapeutic Targets Database DAP000291 Link_out
PharmGKB PA449484 Link_out
Drug Product Database 2017598 Link_out
RxList http://www.rxlist.com/cgi/generic/ergocalciferol.htm Link_out
Drugs.com http://www.drugs.com/cdi/ergocalciferol.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/vit_0265.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Ergocalciferol Link_out
ATC Codes
  • A11CC01
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (78.4 KB)
Interactions
Drug Interactions
Drug Interaction
Cholecalciferol Vitamin D analogs may enhance the adverse/toxic effect of other Vitamin D analogs. Avoid combined use of multiple vitamin D analogs (at pharmacologic doses). Prescribing information for calcitriol, doxercalciferol, paricalcitol, and alfacalcidol each specifically cautions against such combined use. Though not specified in the prescribing information for calcipotriene, cholecalciferol, and ergocalciferol, each contains warnings regarding the potential for vitamin D toxicity.
Colesevelam Bile acid sequestrants such as colesevelam may decrease the serum concentration of Vitamin D Analogs. More specifically, bile acid sequestrants may impair absorption of Vitamin D Analogs. Avoid concomitant administration of vitamin D analogs and bile acid sequestrants (e.g., cholestyramine). Monitor plasma calcium concentrations in patients receiving combined therapy with these agents. This is particularly important in patients receiving higher doses of a bile acid sequestant (i.e., 30 g/day or more of cholestyramine or equivalent) or in patients experiencing bile acid sequestrant-induced steatorrhea. Specific recommendations regarding the separation of administration of these agents are not defined; however, it would seem prudent to separate the administration of these agents by several hours to minimize the potential risk of interaction. Similar precautions do not apply to parenterally administered vitamin D analogs.
Food Interactions Not Available
Targets

1. Vitamin D3 receptor

Pharmacological action: yes
Actions: agonist

Nuclear hormone receptor. VDR mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes

Organism class: human
UniProt ID: P11473 Link_out
Gene: VDR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Carvallo L, Henriquez B, Olate J, van Wijnen AJ, Lian JB, Stein GS, Onate S, Stein JL, Montecino M: The 1alpha,25-dihydroxy Vitamin D3 receptor preferentially recruits the coactivator SRC-1 during up-regulation of the osteocalcin gene. J Steroid Biochem Mol Biol. 2007 Mar;103(3-5):420-4. Epub 2007 Jan 10. Pubmed
  2. Liu W, Tretiakova M, Kong J, Turkyilmaz M, Li YC, Krausz T: Expression of vitamin D3 receptor in kidney tumors. Hum Pathol. 2006 Oct;37(10):1268-78. Epub 2006 Jul 27. Pubmed
  3. Ewing AK, Attner M, Chakravarti D: Novel regulatory role for human Acf1 in transcriptional repression of vitamin D3 receptor-regulated genes. Mol Endocrinol. 2007 Aug;21(8):1791-806. Epub 2007 May 22. Pubmed
  4. Gallagher JC, Sai AJ: Vitamin D insufficiency, deficiency, and bone health. J Clin Endocrinol Metab. 2010 Jun;95(6):2630-3. Pubmed
  5. Straube S, Derry S, Moore RA, McQuay HJ: Vitamin D for the treatment of chronic painful conditions in adults. Cochrane Database Syst Rev. 2010 Jan 20;(1):CD007771. Pubmed
  6. Jurutka PW, Bartik L, Whitfield GK, Mathern DR, Barthel TK, Gurevich M, Hsieh JC, Kaczmarska M, Haussler CA, Haussler MR: Vitamin D receptor: key roles in bone mineral pathophysiology, molecular mechanism of action, and novel nutritional ligands. J Bone Miner Res. 2007 Dec;22 Suppl 2:V2-10. Pubmed
  7. Mikhak B, Hunter DJ, Spiegelman D, Platz EA, Hollis BW, Giovannucci E: Vitamin D receptor (VDR) gene polymorphisms and haplotypes, interactions with plasma 25-hydroxyvitamin D and 1,25-dihydroxyvitamin D, and prostate cancer risk. Prostate. 2007 Jun 15;67(9):911-23. Pubmed
  8. Marks HD, Fleet JC, Peleg S: Transgenic expression of the human Vitamin D receptor (hVDR) in the duodenum of VDR-null mice attenuates the age-dependent decline in calcium absorption. J Steroid Biochem Mol Biol. 2007 Mar;103(3-5):513-6. Epub 2007 Jan 5. Pubmed
  9. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Enzymes

1. Cytochrome P450 24A1, mitochondrial

Actions: substrate

Has a role in maintaining calcium homeostasis. Catalyzes the NADPH-dependent 24-hydroxylation of 25-hydroxyvitamin D(3) in the presence of adrenodoxin and NADPH-adrenodoxin reductase

UniProt ID: Q07973 Link_out
Gene: CYP24A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Masuda S, Strugnell SA, Knutson JC, St-Arnaud R, Jones G: Evidence for the activation of 1alpha-hydroxyvitamin D2 by 25-hydroxyvitamin D-24-hydroxylase: delineation of pathways involving 1alpha,24-dihydroxyvitamin D2 and 1alpha,25-dihydroxyvitamin D2. Biochim Biophys Acta. 2006 Feb;1761(2):221-34. Epub 2006 Feb 2. Pubmed
  2. Sakaki T, Kagawa N, Yamamoto K, Inouye K: Metabolism of vitamin D3 by cytochromes P450. Front Biosci. 2005 Jan 1;10:119-34. Print 2005 Jan 1. Pubmed
  3. Abe D, Sakaki T, Kusudo T, Kittaka A, Saito N, Suhara Y, Fujishima T, Takayama H, Hamamoto H, Kamakura M, Ohta M, Inouye K: Metabolism of 2 alpha-propoxy-1 alpha,25-dihydroxyvitamin D3 and 2 alpha-(3-hydroxypropoxy)-1 alpha,25-dihydroxyvitamin D3 by human CYP27A1 and CYP24A1. Drug Metab Dispos. 2005 Jun;33(6):778-84. Epub 2005 Mar 11. Pubmed
  4. Sakaki T: [Recent studies on vitamin D metabolizing enzymes] Clin Calcium. 2006 Jul;16(7):1129-35. Pubmed
  5. Inouye K, Sakaki T: Enzymatic studies on the key enzymes of vitamin D metabolism; 1 alpha-hydroxylase (CYP27B1) and 24-hydroxylase (CYP24). Biotechnol Annu Rev. 2001;7:179-94. Pubmed

2. 25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial

Actions: substrate

Catalyzes the conversion of 25-hydroxyvitamin D3 (25(OH)D) to 1-alpha,25-dihydroxyvitamin D3 (1,25(OH)2D) plays an important role in normal bone growth, calcium metabolism, and tissue differentiation

UniProt ID: O15528 Link_out
Gene: CYP27B1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Turunen MM, Dunlop TW, Carlberg C, Vaisanen S: Selective use of multiple vitamin D response elements underlies the 1 alpha,25-dihydroxyvitamin D3-mediated negative regulation of the human CYP27B1 gene. Nucleic Acids Res. 2007;35(8):2734-47. Epub 2007 Apr 10. Pubmed
  2. Gallagher JC, Sai AJ: Vitamin D insufficiency, deficiency, and bone health. J Clin Endocrinol Metab. 2010 Jun;95(6):2630-3. Pubmed
  3. Sakaki T, Kagawa N, Yamamoto K, Inouye K: Metabolism of vitamin D3 by cytochromes P450. Front Biosci. 2005 Jan 1;10:119-34. Print 2005 Jan 1. Pubmed
  4. Sakaki T: [Recent studies on vitamin D metabolizing enzymes] Clin Calcium. 2006 Jul;16(7):1129-35. Pubmed
  5. Inouye K, Sakaki T: Enzymatic studies on the key enzymes of vitamin D metabolism; 1 alpha-hydroxylase (CYP27B1) and 24-hydroxylase (CYP24). Biotechnol Annu Rev. 2001;7:179-94. Pubmed

3. Cytochrome P450 27, mitochondrial

Actions: substrate

Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta- cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3- 25-hydroxylase activity

UniProt ID: Q02318 Link_out
Gene: CYP27A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Binkley N, Ramamurthy R, Krueger D: Low vitamin D status: definition, prevalence, consequences, and correction. Endocrinol Metab Clin North Am. 2010 Jun;39(2):287-301, table of contents. Pubmed
  2. Masuda S, Strugnell SA, Knutson JC, St-Arnaud R, Jones G: Evidence for the activation of 1alpha-hydroxyvitamin D2 by 25-hydroxyvitamin D-24-hydroxylase: delineation of pathways involving 1alpha,24-dihydroxyvitamin D2 and 1alpha,25-dihydroxyvitamin D2. Biochim Biophys Acta. 2006 Feb;1761(2):221-34. Epub 2006 Feb 2. Pubmed
  3. Sakaki T, Kagawa N, Yamamoto K, Inouye K: Metabolism of vitamin D3 by cytochromes P450. Front Biosci. 2005 Jan 1;10:119-34. Print 2005 Jan 1. Pubmed
  4. Abe D, Sakaki T, Kusudo T, Kittaka A, Saito N, Suhara Y, Fujishima T, Takayama H, Hamamoto H, Kamakura M, Ohta M, Inouye K: Metabolism of 2 alpha-propoxy-1 alpha,25-dihydroxyvitamin D3 and 2 alpha-(3-hydroxypropoxy)-1 alpha,25-dihydroxyvitamin D3 by human CYP27A1 and CYP24A1. Drug Metab Dispos. 2005 Jun;33(6):778-84. Epub 2005 Mar 11. Pubmed
  5. Sakaki T: [Recent studies on vitamin D metabolizing enzymes] Clin Calcium. 2006 Jul;16(7):1129-35. Pubmed

4. Cytochrome P450 3A4

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Binkley N, Ramamurthy R, Krueger D: Low vitamin D status: definition, prevalence, consequences, and correction. Endocrinol Metab Clin North Am. 2010 Jun;39(2):287-301, table of contents. Pubmed

5. Cytochrome P450 2R1

Actions: substrate

Has a D-25-hydroxylase activity on both forms of vitamin D, vitamin D(2) and D(3)

UniProt ID: Q6VVX0 Link_out
Gene: CYP2R1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ramos-Lopez E, Bruck P, Jansen T, Pfeilschifter JM, Radeke HH, Badenhoop K: CYP2R1-, CYP27B1- and CYP24-mRNA expression in German type 1 diabetes patients. J Steroid Biochem Mol Biol. 2007 Mar;103(3-5):807-10. Epub 2007 Jan 16. Pubmed
  2. Ramos-Lopez E, Bruck P, Jansen T, Herwig J, Badenhoop K: CYP2R1 (vitamin D 25-hydroxylase) gene is associated with susceptibility to type 1 diabetes and vitamin D levels in Germans. Diabetes Metab Res Rev. 2007 Jul 2;. Pubmed
  3. Masuda S, Strugnell SA, Knutson JC, St-Arnaud R, Jones G: Evidence for the activation of 1alpha-hydroxyvitamin D2 by 25-hydroxyvitamin D-24-hydroxylase: delineation of pathways involving 1alpha,24-dihydroxyvitamin D2 and 1alpha,25-dihydroxyvitamin D2. Biochim Biophys Acta. 2006 Feb;1761(2):221-34. Epub 2006 Feb 2. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19